The Personal Strategic Plan Inspired By a Harvard Business Legend

This five-step personal strategic planning exercise applies best practices from the business world to your life.


One of my favorite books I’ve read in the last while is How Will You Measure Your Life?

In it, Harvard Business School strategy guru Clayton Christensen applies his world-renowned theories to the business of living a good life. And he tries to understand why so many successful CEOs he’s known ran their personal lives to the ground.

The biggest reason?

Self-help-ing yourself is way more boring than making billions.

Big shot CEOs strategize business moves in meetings all day long, but never bother with any semblance of a personal strategic plan. Eventually, they became miserable.

Christensen convinced me to try not to make the same mistake. So I followed the advice from his book and others like it—The 7 Habits of Highly Successful People, especially—to devise a personal strategic plan of my own.

I call it the “GPS” (general personal strategy).

It’s a five-step template that’s helped me figure out how to redirect my life toward not billions of dollars but fewer regrets and more good times.

General Personal Strategy (GPS) for [Insert Your Name Here]

To maximize My Life’s returns to (Step 1), I will optimize for (Step 2) and do some good by battling (Step 3). To do so more productively, I will release my handbrake of (Step 4.1) and replace it with (Step 4.2). And I am starting work on all of this immediately by (Step 5).

Personal Strategic Plan Step #1:

Think of your shareholders.

If you’re the CEO of Your Life, Inc., you’re the head honcho responsible for delivering results to your shareholders.

Who are your shareholders?

Unless you got a bit ahead of yourself with the whole NFT craze and sold shares of yourself online, I’d argue your shareholders aren’t other people. Not even your kids or wife.

Your shareholders are future versions of you.

Imagine each Future You for every day left in your life has one voting share. They want themselves and the people they care about to be happy.

Then ask yourself:

What action would the largest number of your thousands of shareholders vote in favor of?

Keep in mind that your shareholders know what you’re incapable of. They won’t expect you to change the world in a day. Plus, they don’t want you to work so hard that it makes them miserable when it’s their turn to take the reins.

And today, it’s your turn. To be a better CEO, just try to be less selfish and more shareholder-friendly.

Then tomorrow, hopefully the next version of you takes over and does the same.

YouTube video

Personal Strategic Plan Step #2:

Define your KPI.

Ok, so you want to maximize returns to your future selves, a.k.a. your shareholders.

What KPI (key performance indicator) are you using to measure how good or bad of a job you’re doing?

Consider this chart roughly approximating your life’s performance to date:

Your “Max Potential” is the absolute highest return you can deliver to your shareholders. Time is your x-axis. And the big question is:

What’s your y-axis?

Happiness? Balance? Sense of community? Freedom? Buckets of Häagen-Dasz consumed?

There’s no easy answer. There’s not even a definitively correct answer. But it shouldn’t be impossible for you to come up with something better than what our monkey minds default to: money, sex, and power.

Even a rough KPI for your y-axis will help you make better long-run decisions. When in doubt, use it to ask yourself:

What action will direct me higher up my y-axis?

For example, I think my y-axis is “Growth.” So, by prioritizing growth over money, I decided to challenge myself to write this post instead of some money-grubbing article like, “Why starting a blog by using all these links that earn me money will get you the passive-income life of your dreams.”

Personal Strategic Plan Step #3:

Pick your battle.

This personal strategic planning step is triply counterintuitive, so lots of people skip it or screw it up.

Counter-intuition #1: To enjoy life, you need to struggle.

Without conflict, the story of your life will have no plot. And, as Donald Miller puts it in one of my favorite “sledgehammer” books, “If you aren’t telling a good story, nobody thinks you died too soon; they just think you died.”

To make matters worse, if you don’t pick your struggles, struggles you don’t want will find you.

Counter-intuition #2; Happiness doesn’t come from trying to make yourself happy but as a by-product of helping others get happier.

This is called the Hedonistic Paradox.

My favorite question for dealing with it and figuring out in what way you can help yourself by helping others is this:

What’s an injustice in the world that pisses you off and you’re willing and able to take on?

Counter-intuition #3: The best battles to pick are the ones you cannot win.

Rather than pick some dragon to slay, mountain to climb, or step-mom to hate, lick your finger, stick it in the air, and look for a headwind. It probably won’t ever stop blowing in your face, but you can harness it to make meaningful progress against it while enjoying the ride.

My battle, for example, is with the status quo and the social pressures and forces of complacency that support it. I’ll never defeat the status quo, but I’ve been having a wicked good time taking it on so far. And I like to think some people have benefitted from it.

What do you think your battle could be?

Cover image of me finding and releasing self-limiting beliefs
If only finding your handbrake of a self-limiting belief were so easy.

Personal Strategic Plan Step #4:

Release your handbrake.

After the first three pie-in-the-sky steps of your personal strategic planning, it’s time to bring things back down to earth with this question:

What self-limiting belief holds you back from making more efficient progress?

This is your handbrake. Release it and your life will flow much more smoothly.

Step 4.1: Identify the limiting identity that’s your biggest handbrake.

Try these handbrake diagnostinacators:

  • What’s the most hurtful insult someone can give you?
    • e.g., If it stings when someone says, “You’re a coward,” it’s probably true. Or maybe you’re protecting some limiting identity of being perfect or successful by not taking more risks.
  • What fixed mindset could you replace with a growth mindset?
    • e.g., Thinking, “I’m smart.” That will make you defensive to evidence that you’re wrong and lead you to avoid challenging your self-perceived intelligence. Better to identify as “someone who likes to learn.”
  • When do you catch yourself saying, “I’m not _____ enough,” “I’m too
  • _____,”  or “I suck at ______”?
    • e.g., “I’m too old to take on a personal strategic plan” means your age has become a limiting identity for you.

Step 4.2: Find an accelerating identity to put in its place.

A good accelerating identity:

  • Pushes you forward rather than holds you back.
  • Is inconsistent with the limiting identity you’re releasing.
  • Expands your potential rather than restricts it.
  • Is something you genuinely believe you can live up to.

The last point’s worth emphasizing. No matter how many positive affirmations you perform, you can’t “be anything you want.” You’re not that genetically gifted.

For example, a limiting identity I used to have is “I’m antisocial.” Positively affirming, “I’m a people person,” in the mirror ten times every morning would never have worked. The more realistic maximizing identity that’s done the trick is to focus on being more of something I already was: “fun to be around.”

Now your turn. Come up with answers to Steps 4.1 and 4.1 and fill in the blanks:

I’m not going to be _____ anymore. I’m _____.

Personal Strategic Plan Step #5:

Stop planning and get started.

Your personal strategic plan is nothing more than self-help fantasizing without this step.

Get your head out of your butt and get moving by asking yourself:

What one small daily habit can you easily make the time to commit to doing to make your plan a reality?

To find your answer, let’s break this question down:

  • What one… What’s the single action you want to start with? Stick to one thing. Then, only when your comfort zone has expanded around it, add another. And so on. Keep it up and, before you know it, you’ll have incorporated dozens of improvements, and your comfort zone will be enormous.
  • …small daily habit…: What’s something so easy you could commit to keeping up for a whole year? Increase your odds of success by simply trying to do it for a week or two. One month, max.
  • …can you easily make the time…: What will you quit doing to free up time and energy for this new action?
  • …to commit to doing…: When will you stop to assess whether or not this habit is moving you in the right direction? Be prepared to change direction instead of putting your head down until you smash into a dead end.
  • …to make your plan a reality: What habit contributes toward steps 1, 2, 3, and 4? Be consistent and coherent to be productive.

Once you have something in mind, ask yourself, “How can I make this 10 percent more fun?” Do it with friends? Plan a celebration after doing it for a month?

Some plan is better than no plan.

Once again, here’s the GPS template:

GPS for [Insert Your Name Here]

To optimize my life’s returns to my shareholders (Step 1), I will optimize for (Step 2) and do some good by battling (Step 3). To do so more productively, I will release my handbrake of (Step 4.1) and replace it with (Step 4.2). And I am starting work on all of this immediately by (Step 5).

Whether or not you decide to use this format doesn’t matter. It’s not like every CEO follows the same strategy, after all. You’re in charge of figuring out what works for you.

But, for your shareholders’ sake, hopefully the questions and explanations of each of the five steps have inspired you to prepare a personal strategic plan of your own. Better yet, read How Will You Measure Your Life.

Just plan something. As long as you devise a strategy that gives you a slightly better sense of direction than before, and move on it, that’s progress.

How Will You Measure Your Life, by Clayton Christensen

Cover image photo of Clayton Christensen adapted from Flickr.

Free Wake-Up Call

Take the 20-question "Comfort Zone Assessment" to find out in just 3.5 minutes:

Where are you complacent?

Which area of your life most needs a push?

How to get started?

It's gimmicky and unscientific, but also quick, fun, and revealing.

Be Uncomplacent

PS: Surprise personalized accountability challenge afterward.

About the author

I'm Chris. Canadian, husband, dad, writer, investor, athlete, and obsessed explorer of the secrets to living a never-boring, always improving, unfollowable life story.

Leave a Comment

Latest Articles

Slide Some Excitement Into Your Inbox

Join me and 5,000 others for a weekly dose of uncomplacent, unconventional inspiration for enjoying life on your own terms.